1,1,1-Trifluoro-2-methylpropan-2-ol → 4-Nitrophenyl 1,1,1-Trifluoro-2-Methylpropan-2-yl-carbonate

HRID 452861

Reaktionsgleichung

Reaktionsgleichung von HRID 452861
[F:1][C:2]([F:8])([F:7])[C:3]([CH3:6])([OH:5])[CH3:4].C([Li])CCC.Cl[C:15]([O:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)=[O:16]>C1COCC1.CCCCCC.C(OCC)(=O)C>[C:15](=[O:16])([O:5][C:3]([CH3:6])([CH3:4])[C:2]([F:8])([F:7])[F:1])[O:17][C:18]1[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=1

Komponenten

7

Edukt 3

HCID 681821,1,1-Trifluoro-2-methylpropan-2-olHCID 821294-Nitrophenyl chloroformateHCID 178418339Butyllithium

Produkt 1

HCID 577851834-Nitrophenyl 1,1,1-Trifluoro-2-Methylpropan-2-yl-carbonate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 1,1,1-trifluoro-2-methylpropan-2-ol (1.0 g) in THF (30 ml) was added a 2M solution of n-butyl lithium in n-hexane (3.9 ml) and then 4-nitrophenyl chloroformate (2.4 g) at −75° C. The mixture was warmed to room temperature and diluted with ethyl acetate, washed with water, dried over sodium sulfate, and filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (0-50% EtOAc/Hexane) to give 4-nitrophenyl 1,1,1-trifluoro-2-methylpropan-2-yl carbonate as a pale yellow oil.

Aufarbeitung

  1. customat −75° C
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (0-50% EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d226a86c646a4f2c83cd6e94dc8b76d3
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492397B2

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